Classification categories, such as those indicating sensitivity of information contained in files or classified nature of files, may be used in computing systems to protect the contents of the files. For instance, data leakage protection technologies may use classification categories with which files are associated to provide real-time prevention of data leaks (unauthorized access of the files). That is, data leakage protection technologies may attempt to protect classified files when unauthorized access of the classified files are about to take place. Such technologies provide incomplete protection of classified files. For example, such technologies do not account for risk of data leakage prior to data leaking event, facilitate preventative actions prior to data leaking events, or effectively provide for analysis of data leaking events.